KR20170043920A - Photosensitive resin composition, photosensitive resin film using the same and color filter - Google Patents

Abstract

The present invention provides a photosensitive resin composition, a photosensitive resin film produced using the same, and a color filter comprising the photosensitive resin film, wherein the photosensitive resin composition comprises: (A) a binder resin; (B) a pigment including a cation and an anion; (C) a photopolymerizable compound; (D) a photopolymerization initiator; and (E) a solvent, wherein the pigment is included in 15-40 wt% with respect to the total weight of the photosensitive resin composition, and the cation is represented by chemical formula 1. In the chemical formula 1, each of the substituents is as defined in the specification.

Description

TECHNICAL FIELD [0001] The present invention relates to a photosensitive resin composition, a photosensitive resin film, and a color filter using the same. BACKGROUND ART [0002]

The present invention relates to a photosensitive resin composition, a photosensitive resin film using the same, and a color filter.

In order to facilitate the stable dispersion and fineness of the pigment dispersion, various studies have been conducted to make pigments having a particle size of a certain size through a process such as salt milling of the pigment obtained through synthesis. Further, in the case of a pigment, there is a limit of brightness and contrast ratio resulting from particle size, and in the case of a color imaging device for an image sensor, a smaller dispersion particle size is required for forming a fine pattern. Therefore, Studies have been made to improve physical properties such as brightness and contrast ratio by using a hybrid type colorant in which a pigment and a dye are mixed.

However, up to now, no coloring agent has been reported which has a greater effect of improving physical properties such as heat resistance and brightness as compared with conventional coloring agents and the like.

Therefore, it is necessary to study a coloring agent used in the production of a photosensitive resin composition, particularly a compound suitable as a dye.

One embodiment is to provide a photosensitive resin composition.

Another embodiment is to provide a photosensitive resin film produced using the photosensitive resin composition.

Another embodiment is to provide a color filter comprising the photosensitive resin film.

One embodiment includes (A) a binder resin; (B) a dye consisting of a cation and an anion; (C) a photopolymerizable compound; (D) a photopolymerization initiator and (E) a solvent, wherein the dye is contained in an amount of 15% by weight to 40% by weight based on the total amount of the photosensitive resin composition, and the cation is represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁶ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group,

R ⁷ is a substituted or unsubstituted C6 to C20 aryl group,

X is -O-, -S- or -NR ⁸ - (R ⁸ is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group).

X may be -O- or -S-.

Each of R ¹ to R ⁴ independently represents a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

The cation may be represented by the following formula (2).

(2)

In Formula 2,

R ⁹ and R ¹⁰ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ¹¹ and R ¹² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,

R ¹³ is a substituted or unsubstituted C6 to C20 aryl group,

R ¹⁴ to R ¹⁷ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

n1 to n4 each independently represent an integer of 0 to 5, 0? n1 + n2? 5, 0? n3 + n4? 5,

X is -O- or -S-.

The cation may be represented by any one selected from the group consisting of the following Chemical Formulas (3) to (7).

(3)

In Formula 3,

R ¹⁸ , R ¹⁹ and R ²¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ²² is a halogen atom,

R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

m is an integer of 0 to 2,

n5 to n8 each independently represent an integer of 0 or 1,

X is -O- or -S-.

[Chemical Formula 4]

In Formula 4,

R ¹⁸ to R ²¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ²² is a halogen atom,

R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

m is an integer of 0 to 2,

n5 to n8 each independently represent an integer of 0 or 1,

X is -O- or -S-.

[Chemical Formula 5]

In Formula 5,

R ¹⁸ and R ¹⁹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ²² is a halogen atom,

R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

R ²⁷ is a substituted or unsubstituted C6 to C20 aryl group,

m is an integer of 0 to 2,

n5 to n8 each independently represent an integer of 0 or 1,

X is -O- or -S-.

[Chemical Formula 6]

In Formula 6,

R ¹⁸ and R ¹⁹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ²² is a halogen atom,

R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

R ²⁷ and R ²⁸ are each independently a substituted or unsubstituted C6 to C20 aryl group,

m is an integer of 0 to 2,

n5 to n8 each independently represent an integer of 0 or 1,

X is -O- or -S-.

(7)

In Formula 7,

R ¹⁸ , R ¹⁹ and R ²¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ²² is a halogen atom,

R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

R ²⁸ is a substituted or unsubstituted C6 to C20 aryl group,

m is an integer of 0 to 2,

n5 to n8 each independently represent an integer of 0 or 1,

X is -O- or -S-.

The cations are represented by the following formulas (5-3), (5-4), (5-5), (5-6), (7-6), (7-8), (7-10), (7-12) 7-17. ≪ / RTI >

[Formula 5-3]

[Formula 5-4]

[Formula 5-5]

[Formula 5-6]

[Formula 7-6]

[Formula 7-8]

[Formula 7-10]

[Formula 7-12]

[Chemical Formula 7-14]

[Formula 7-17]

The anion may be represented by any one selected from the group consisting of the following chemical formulas (A) to (F).

(A)

[Chemical Formula B]

≪ RTI ID = 0.0 &

PW ₁₂ O ₄₀ ^{3 -}

[Chemical Formula D]

SiW ₁₂ O ₄₀ ^{4 -}

(E)

CF ₃ SO ₃ ^-

[Chemical Formula F]

ClO ₄ ^-

The dye may be a blue dye.

The dye may have a maximum absorbance (? _Max ) in the wavelength range of 600 nm to 700 nm.

The dye may have a maximum transmittance (T _max ) in the wavelength range of 400 nm to 500 nm.

The photosensitive resin composition may further comprise a pigment.

The binder resin may have a weight average molecular weight of 5,000 g / mol to 15,000 g / mol.

The binder resin may have an acid value of 80 mgKOH / g to 130 mgKOH / g.

The binder resin may include an acrylic binder resin, a cadmium binder resin, or a combination thereof.

Wherein the photosensitive resin composition comprises 1 to 30% by weight of the binder resin (A) relative to the total amount of the photosensitive resin composition; 10% to 40% by weight of the dye (B); 1 to 15% by weight of the (C) photopolymerizable compound; 0.01 to 10% by weight of the photopolymerization initiator (D) and the remaining amount of the solvent (E).

The photosensitive resin composition may further include additives such as an epoxy compound, malonic acid, 3-amino-1,2-propanediol, a silane coupling agent, a leveling agent, a surfactant, a radical polymerization initiator or a combination thereof.

Another embodiment provides a photosensitive resin film produced using the photosensitive resin composition.

Another embodiment provides a color filter comprising the photosensitive resin film.

Other aspects of the present invention are included in the following detailed description.

The photosensitive resin composition according to one embodiment can contain a dye having excellent coloring power within a specific content range, and can manufacture a color filter excellent in luminance, heat resistance, chemical resistance, and light resistance.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

Means that at least one hydrogen atom of the functional group of the present invention is substituted with a halogen atom (F, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amino group NH _2, NH (R ^200), or N (R ²⁰¹⁾ (R ^202), wherein R ^200, R ²⁰¹ and R ²⁰² are the same or different, each independently being a C1 to C10 alkyl groups), amidino group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, and a substituted or unsubstituted heterocyclic group.

Unless otherwise specified in the specification, "alkyl group" means C1 to C20 alkyl group, specifically C1 to C15 alkyl group, "cycloalkyl group" means C3 to C20 cycloalkyl group, specifically C3 Refers to a C1 to C20 alkoxy group, specifically, a C1 to C18 alkoxy group, and an "aryl group" means a C6 to C20 aryl group, specifically, a C6 to C20 aryl group, Refers to a C 2 to C 20 alkenyl group, specifically, a C 2 to C 18 alkenyl group, and the "alkylene group" refers to a C 1 to C 20 alkylene group, specifically, a C1 Refers to a C6 to C20 arylene group, and specifically refers to a C6 to C16 arylene group.

(Meth) acrylate "refers to both" acrylic acid "and" methacrylic acid " It means both are possible.

As used herein, unless otherwise defined, "combination" means mixing or copolymerization. "Copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.

Unless otherwise defined in the chemical formulas in this specification, when no chemical bond is drawn at the position where the chemical bond should be drawn, it means that the hydrogen atom is bonded at the above position.

Unless otherwise defined herein, "*" means the same or different atom or moiety connected to a formula.

The photosensitive resin composition according to one embodiment comprises (A) a binder resin; (B) a dye consisting of a cation and an anion; (C) a photopolymerizable compound; (D) a photopolymerization initiator and (E) a solvent, wherein the dye is contained in an amount of 15% by weight to 40% by weight based on the total amount of the photosensitive resin composition, and the cation is represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R ¹ to R ⁶ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group,

R ⁷ is a substituted or unsubstituted C6 to C20 aryl group,

X is -O-, -S- or -NR ⁸ - (R ⁸ is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group).

The photosensitive resin composition according to one embodiment contains 15 to 40% by weight of a dye composed of a cation and an anion represented by the formula (1) based on the total amount of the photosensitive resin composition. When the dye is included in the content range , A compound used as an existing colorant such as a triarylmethane compound, has excellent spectroscopic characteristics and a high molar extinction coefficient, is excellent in coloring power and heat resistance, and has excellent solubility in organic solvents such as cyclohexanone and PGMEA do. In particular, the cation represented by the formula (1) has three rings connected to the central carbon. Since one of the three rings has an aromatic heterocyclic ring containing a cyano group, the cation and anion Can provide a color filter excellent in luminance, heat resistance, chemical resistance, and light resistance.

Each component will be described in detail below.

(B) Dye

As described above, the photosensitive resin composition according to one embodiment includes a dye composed of a cation and an anion, and the cation is represented by the above formula (1).

For example, X may be -O- or -S-.

For example, each of R ¹ to R ⁴ may independently be a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

In recent years, in order to produce a color filter excellent in heat resistance, light resistance, and chemical resistance while having a high luminance, a dye having excellent durability is prepared, and a composition containing the dye is used to produce a color filter having high brightness, heat resistance, And chemical resistance are being actively studied. Particularly, studies using triarylmethane compounds known as blue dyes among the above dyes have been carried out. The triarylmethane dye has an advantage that it has a high luminance in a wavelength range of 420 nm to 450 nm, but has a disadvantage in that it has poor solubility in an organic solvent such as PGMEA and has poor heat resistance, light resistance and chemical resistance. In order to overcome weak heat resistance, attempts have been made to use anions such as naphthalenesulfonic acid and naphthylamine sulfonic acid in triarylmethane dyes, but heat resistance and the like have not been greatly improved.

The dyes contained in the composition according to one embodiment have excellent spectroscopic characteristics and a high molar extinction coefficient as compared with dye compounds such as triarylmethane compounds used as conventional colorants, including cations represented by the formula (1) Heat resistance, light resistance, chemical resistance, and solubility in organic solvents such as cyclohexanone and PGMEA. In particular, the dye contained in the composition according to one embodiment has three rings linked to the central carbon, wherein one ring of the three rings has an aromatic heterocycle comprising a cyano group, Can provide a color filter excellent in heat resistance, light resistance, and chemical resistance together with high brightness.

For example, the cation may be represented by the following formula (2).

(2)

In Formula 2,

R ⁹ and R ¹⁰ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ¹¹ and R ¹² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,

R ¹³ is a substituted or unsubstituted C6 to C20 aryl group,

R ¹⁴ to R ¹⁷ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

n1 to n4 each independently represent an integer of 0 to 5, 0? n1 + n2? 5, 0? n3 + n4? 5,

X is -O- or -S-.

For example, n1 to n4 may each independently be an integer of 0 or 1.

For example, the halogen atom may be F, Cl, Br or I.

For example, the cation may be represented by any one selected from the group consisting of the following Chemical Formulas (3) to (7).

(3)

In Formula 3,

R ¹⁸ , R ¹⁹ and R ²¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ²² is a halogen atom,

R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

m is an integer of 0 to 2,

n5 to n8 each independently represent an integer of 0 or 1,

X is -O- or -S-.

[Chemical Formula 4]

In Formula 4,

R ¹⁸ to R ²¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ²² is a halogen atom,

R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

m is an integer of 0 to 2,

n5 to n8 each independently represent an integer of 0 or 1,

X is -O- or -S-.

[Chemical Formula 5]

In Formula 5,

R ¹⁸ and R ¹⁹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ²² is a halogen atom,

R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

R ²⁷ is a substituted or unsubstituted C6 to C20 aryl group,

m is an integer of 0 to 2,

n5 to n8 each independently represent an integer of 0 or 1,

X is -O- or -S-.

[Chemical Formula 6]

In Formula 6,

R ¹⁸ and R ¹⁹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ²² is a halogen atom,

R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

R ²⁷ and R ²⁸ are each independently a substituted or unsubstituted C6 to C20 aryl group,

m is an integer of 0 to 2,

n5 to n8 each independently represent an integer of 0 or 1,

X is -O- or -S-.

(7)

In Formula 7,

R ¹⁸ , R ¹⁹ and R ²¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ²² is a halogen atom,

R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

R ²⁸ is a substituted or unsubstituted C6 to C20 aryl group,

m is an integer of 0 to 2,

n5 to n8 each independently represent an integer of 0 or 1,

X is -O- or -S-.

For example, the cation may be represented by the following formulas (3-1), (3-2), (4-1) to (4-3), (5-1) to (5-8), (6-1) To (7-17), but the present invention is not limited thereto.

[Formula 3-1]

[Formula 3-2]

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

[Formula 5-4]

[Formula 5-5]

[Formula 5-6]

[Formula 5-7]

[Formula 5-8]

[Formula 6-1]

[Formula 6-2]

[Formula 6-3]

[Formula 6-4]

[Formula 6-5]

[Formula 6-6]

[Formula 6-7]

[Formula 6-8]

[Formula 6-9]

[Chemical Formula 6-10]

[Chemical Formula 6-11]

[Chemical Formula 6-12]

[Formula 6-13]

[Chemical Formula 6-14]

[Chemical Formula 6-15]

[Chemical Formula 6-16]

[Chemical Formula 6-17]

[Chemical Formula 6-18]

[Chemical Formula 6-19]

[Formula 7-1]

[Formula 7-2]

[Formula 7-3]

[Chemical Formula 7-4]

[Formula 7-5]

[Formula 7-6]

[Formula 7-7]

[Formula 7-8]

[Formula 7-9]

[Formula 7-10]

[Formula 7-11]

[Formula 7-12]

[Formula 7-13]

[Chemical Formula 7-14]

[Chemical Formula 7-15]

[Chemical Formula 7-16]

[Formula 7-17]

The compound according to an embodiment includes an anion, and the anion may be represented by any one selected from the group consisting of the following formulas (A) to (F), but is not limited thereto.

(A)

[Chemical Formula B]

≪ RTI ID = 0.0 &

PW ₁₂ O ₄₀ ^{3 -}

[Chemical Formula D]

SiW ₁₂ O ₄₀ ^{4 -}

(E)

CF ₃ SO ₃ ^-

[Chemical Formula F]

ClO ₄ ^-

The dyes contained in the composition according to one embodiment include the cations represented by the formula (1), so that a clearer color can be expressed even in a small amount, and when the colorant is used as a colorant, . ≪ / RTI > For example, the dye may be a dye having a maximum absorbance (? _Max ) in a blue dye, for example in the wavelength range of 600 nm to 700 nm, for example in the wavelength range of 630 nm to 670 nm, for example in the wavelength range of 640 nm to 650 nm . For example, the dye may be a dye having a maximum transmittance (T _max ) in a wavelength range of 400 nm to 500 nm, for example, a wavelength range of 420 nm to 450 nm, for example, a wavelength range of 430 nm to 440 nm.

In general, dyes are the most expensive component of the components used in color filters. Therefore, in order to achieve a desired effect, for example, a high luminance and a high contrast ratio, it is necessary to use more expensive dye, so that the production cost has to be increased. However, when the dye contained in the composition according to one embodiment is used as a dye in a color filter, it is possible to achieve excellent color characteristics such as high luminance and high contrast ratio in a small amount, thereby reducing the production cost.

The dye may be contained in an amount of 10% by weight to 40% by weight, for example, 15% by weight to 30% by weight based on the total amount of the photosensitive resin composition. When the compound according to one embodiment is included in the above range, not only color reproducibility and brightness are improved, but also heat resistance, light resistance and chemical resistance are simultaneously excellent .

(B ') pigment

For example, the photosensitive resin composition according to one embodiment may further include a pigment.

The pigments may include, but are not limited to, blue pigments, yellow pigments, green pigments, red pigments, violet pigments, or combinations thereof. For example, the pigment may be included in the photosensitive resin composition in the form of a pigment dispersion.

The pigment dispersion may include a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.

The solid pigment may be present in the pigment dispersion in an amount ranging from 1% to 20%, such as 8% to 20%, such as 15% to 20%, such as 8% to 15% 20% by weight, such as 10% by weight to 15% by weight.

As the dispersing agent, a nonionic dispersing agent, an anionic dispersing agent, a cationic dispersing agent and the like can be used. Specific examples of the dispersing agent include polyalkylene glycols and esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid Salts, alkylamide alkylene oxide adducts, and alkylamines. These may be used singly or in combination of two or more.

DISPERBYK-161, DISPERBYK-160, DISPERBYK-161, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-160 and DISPERBYK-160 of BYK Co., -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 and the like; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400 and EFKA-450 of EFKA Chemical Co., Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000 from Zeneka; Or Ajinomoto's PB711 and PB821.

The dispersing agent may be contained in an amount of 1 to 20% by weight based on the total amount of the pigment dispersion. When the dispersing agent is contained within the above range, the dispersibility of the photosensitive resin composition can be maintained because an appropriate viscosity can be maintained, so that optical, physical and chemical quality can be maintained when the product is applied.

As the solvent for forming the pigment dispersion, ethylene glycol acetate, ethyl cellosolve, propylene glycol monomethyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether and the like can be used.

The pigment dispersion may be contained in an amount of 5% by weight to 30% by weight, for example, 10% by weight to 25% by weight based on the total amount of the photosensitive resin composition. When the pigment dispersion is contained within the above range, it is advantageous in securing a process margin and excellent color reproduction ratio and contrast ratio.

(A) Binder resin

The binder resin may be an acrylic binder resin, a carcass binder resin, or a combination thereof.

The acrylic binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable with the first ethylenically unsaturated monomer, and may be a resin containing at least one acrylic repeating unit.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

The first ethylenically unsaturated monomer may be included in an amount of 5% by weight to 50% by weight, for example, 10% by weight to 40% by weight based on the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These may be used singly or in combination of two or more.

Specific examples of the acrylic binder resin include polybenzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene copolymer, (meth) acrylic acid / benzyl methacrylate (Meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, but are not limited thereto, and they may be used alone or in combination of two or more. Two or more kinds may be used in combination.

The weight average molecular weight of the binder resin may be from 5,000 g / mol to 150,000 g / mol, such as from 5,000 g / mol to 50,000 g / mol, such as from 10,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the binder resin is within the above range, the photosensitive resin composition is excellent in physical and chemical properties, has an appropriate viscosity, and is excellent in adhesion with a substrate in the production of a color filter.

The acid value of the binder resin may be 80 mgKOH / g to 130 mgKOH / g, such as 90 mgKOH / g to 120 mgKOH / g. When the acid value of the binder resin is within the above range, the resolution of the pixel pattern is excellent.

The binder resin may be contained in an amount of 1 wt% to 30 wt%, for example, 10 wt% to 25 wt% with respect to the total amount of the photosensitive resin composition. When the binder resin is contained within the above range, the color filter is excellent in developing property and the crosslinking property is improved, whereby excellent surface smoothness can be obtained.

(C) Photopolymerization  compound

The photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond.

By having the ethylenically unsaturated double bond, the photopolymerizable compound can form a pattern having excellent heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure in the pattern formation step.

Specific examples of the photopolymerizable compound include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol di (Meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate, (Meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethacrylate (Meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolac epoxy (meth) acrylate and the like.

Examples of commercially available products of photopolymerizable compounds are as follows. The (meth) acrylic acid is one example of a polyfunctional ester, doah Gosei Kagaku Kogyo's (primary)社Aronix ^M-101? , Dong M-111 ^? , M-114 ^? Etc; KAYARAD TC-110S from Nihon Kayaku Co., Ltd. ^? , The TC-120S ^? Etc; V-158 of Osaka Yuzagaku Kogyo Co., Ltd. ^? , V-2311 ^? And the like. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei Kagaku Kogyo's Aronix M-210 (Note) ^社? , M-240 ^? , M-6200 ^? Etc; KAYARAD HDDA of Nihon Kayaku Co., Ltd. ^? , Dong HX-220 ^? , R-604 ^? Etc; V-260 of Osaka Yuzagaku Kogyo Co., Ltd. ^? , V-312 ^? , V-335 HP ^? And the like. The (meth) three examples of the polyfunctional ester of acrylic acid, doah Gosei are Aronix M-309 of Kagaku Kogyo (Note) ^社? , M-400 ^? , Dong M-405 ^? , Dong M-450 ^? , M-710 ^? , M-8030 ^? , M-8060 ^? Etc; KAYARAD TMPTA of Nihon Kayaku Co., Ltd. ^? , DPCA-20 ^? , -30 ^? , Dong-60 ^? , -120 ^? Etc; V-295 from Osaka Yukigaya Kogyo Co., Ltd. ^? , -300 ^? , -360 ^? , Dong-GPT ^? , Dong-3PA ^? , -400 ^? And the like. These products may be used alone or in combination of two or more.

The photopolymerizable compound may be treated with an acid anhydride so as to give better developing properties.

The photopolymerizable compound may be contained in an amount of 1 wt% to 15 wt%, for example, 5 wt% to 10 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerizable compound is contained within the above-mentioned range, the pattern forming process sufficiently cures upon exposure to light, which is excellent in reliability and developability in an alkaline developer.

(D) Light curing Initiator

The photopolymerization initiator is an initiator generally used in a photosensitive resin composition, for example, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, a oxime compound, Can be used.

Examples of the acetophenone-based compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropanone, p-butyldichloroacetophenone, 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one.

Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2- Chlorothioxanthone and the like.

Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -Dimethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) , 2-biphenyl 4,6-bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl- (Trichloromethyl) -s-triazine, 2- (4-methoxynaphtho-1-yl) -4,6-bis Bis (trichloromethyl) -6- (4-methoxystyryl) -s-triazine, and the like.

Examples of the oxime compounds include O-acyloxime compounds, 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- ) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, O-ethoxycarbonyl- Etc. may be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin- (4-phenylsulfanylphenyl) -butane-1,2-dione 2-oxime-O-benzoate, 1- -Oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1-one oxime-O-acetate and 1- (4-phenylsulfanylphenyl) Acetate and the like.

The photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, or a nonimidazole compound in addition to the above compounds.

The photopolymerization initiator may be used in combination with a photosensitizer that generates a chemical reaction by absorbing light to be in an excited state and transferring its energy.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate and the like .

The photopolymerization initiator may be contained in an amount of 0.01 wt% to 10 wt%, for example, 0.05 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, the photopolymerization initiator is sufficiently cured upon exposure in the pattern formation step to obtain excellent reliability, and the pattern is excellent in heat resistance, light resistance, chemical resistance, resolution and adhesion, It is possible to prevent the transmittance from being lowered.

(E) Solvent

The solvent may be a material that has compatibility with the dye, the pigment, the binder resin, the photopolymerizable compound, and the photopolymerization initiator but does not react.

Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl ether, methylphenyl ether and tetrahydrofuran; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate and diethyl cellosolve acetate; Carbitols such as methylethylcarbitol, diethylcarbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl- ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; Lactic acid esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate and butyl oxyacetate; Alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate and propyl 2-oxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy- Monooximonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyls such as ethyl methyl propionate; Esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate and methyl 2-hydroxy-3-methylbutanoate; Ketone acid esters such as ethyl pyruvate, and the like, and also include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, And high boiling solvents such as ethyl acetate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

Among them, glycol ethers such as ethylene glycol monoethyl ether and the like are preferably used in consideration of compatibility and reactivity; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as ethyl 2-hydroxypropionate; Carbitols such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.

The solvent may be included in an amount of 30% by weight to 90% by weight, such as 30% by weight to 80% by weight, such as 30% by weight to 70% by weight, based on the total amount of the photosensitive resin composition. When the solvent is contained within the above range, the photosensitive resin composition has an appropriate viscosity, and thus the processability in the production of the color filter is excellent.

(F) Other additives

Meanwhile, the photosensitive resin composition may further include additives such as an epoxy compound, malonic acid, 3-amino-1,2-propanediol, a silane coupling agent, a leveling agent, a surfactant, a radical polymerization initiator, .

Specifically, the photosensitive resin composition may further include an epoxy compound to improve adhesion with the substrate.

Examples of the epoxy compound include a phenol novolak epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.

The epoxy compound may be contained in an amount of 0.01 to 20 parts by weight, for example, 0.1 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is contained within the above range, the adhesiveness and storage stability are excellent.

The photosensitive resin composition may further include a silane-based coupling agent having reactive substituents such as a carboxyl group, a methacryloyl group, an isocyanate group, and an epoxy group in order to improve adhesion with a substrate.

Examples of the silane-based coupling agent include trimethoxysilylbenzoic acid,? -Methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane,? -Isocyanate propyltriethoxysilane,? -Glycine (3,4-epoxycyclohexyl) ethyltrimethoxysilane, etc. These may be used singly or in combination of two or more.

The silane coupling agent may be included in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is contained within the above range, the adhesion and storage stability are excellent.

The above-mentioned photosensitive resin composition may further contain a surfactant for improving coatability and preventing defect formation if necessary.

Examples of the surfactant include BM-1000 ^? , BM-1100 ^? Etc; Dai Nippon Ink Kagaku Kogyo Co., Ltd. Mecha Pack F 142D ^? F 172 ^? F 173 ^? F 183 ^? Etc; Prorad FC-135 from Sumitomo Sri M Co., Ltd. ^? , FC-170C ^? , FC-430 ^? , FC-431 ^? Etc; Saffron S-112 from Asahi Glass Co., Ltd. ^? , S-113 ^? , S-131 ^? , S-141 ^? , S-145 ^? Etc; SH-28PA of Toray Silicone Co., Ltd. ^? , -190 ^? , -193 ^? , SZ-6032 ^? , SF-8428 ^? And the like can be used as the fluorine-based surfactant.

The surfactant may be used in an amount of 0.001 part by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is contained within the above range, uniformity of coating is ensured, no staining occurs, and wetting of the glass substrate is excellent.

The photosensitive resin composition may contain a certain amount of other additives such as an antioxidant and a stabilizer within a range that does not impair the physical properties.

According to another embodiment, there is provided a photosensitive resin film produced using the photosensitive resin composition according to one embodiment.

According to another embodiment, there is provided a color filter comprising the photosensitive resin film.

The pattern forming process in the color filter is as follows.

Applying the photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing or the like; Drying the applied photosensitive resin composition to form a photosensitive resin composition film; Exposing the photosensitive resin composition film; Developing the exposed photosensitive resin composition film with an aqueous alkali solution to produce a photosensitive resin film; And a step of heat-treating the photosensitive resin film. The process conditions and the like are well known in the art, and therefore, detailed description thereof will be omitted herein.

( Example )

(Synthesis of Dye)

Synthetic example  1: Synthesis of dye represented by Formula 7-17-1

After loading the compound (0.71g, 2.1mmol) represented by the following the round bottom flask under a nitrogen atmosphere, a compound (1.03g, 2.1mmol) and represented by the formula 1-2 Formula 2-2 5g toluene and POCl ₃ (1.29 g, 8.4 mmol) was further added, and the temperature was gradually raised to 110 DEG C and stirred for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, extracted with methyl ethyl ketone (MEK), and washed with 10% NaCl, water and 10% HCl. After removal of the organic layer and drying, Lithium bis (trifluormethane) sulfonimide (1.2 g, 4.2 mmol) was added thereto, and 10 g of DMSO was added thereto and stirred at room temperature for 30 minutes (anion exchange process). The stirred reaction product was dropped into water to form a precipitate, which was separated through a filter. The solid compound separated through the filter was dissolved in 40 g of acetonitrile, and 3 g of activated carbon was added thereto, followed by stirring for 30 minutes. The activated carbon was removed through a filter, and the filtrate was removed by distillation and dried to obtain a compound represented by the following formula (7-17-1) (1.90 g, 83%).

[Formula 1-2]

[Formula 2-2]

[Formula 7-17-1]

_{^{1 H NMR (solvent: CDCl 3}} ) 7.51-7.38 (m, 12H), 7.20-7.03 (m, 12H), 6.42 (d, 4H), 4.52-4.45 (m, 2H), 4.08 (q, 2H), 1.38 (t, 3 H), 1.17 (d, 12 H)

Synthetic example  2: Synthesis of the dye represented by the formula 7-14-1

Except that the compound represented by Formula 1-1 and the compound represented by Formula 2-1 were used in place of the compound represented by Formula 1-2 and the compound represented by Formula 2-2 as starting materials, 1, a dye represented by the following formula (7-14-1) was synthesized.

[Formula 1-1]

[Formula 2-1]

[Formula 7-14-1]

_{^{1 H NMR (solvent: CDCl 3}} ) 7.57-7.51 (m, 3H), 7.45-7.26 (m, 8H), 7.10-7.05 (m, 9H), 6.50 (bs, 4H), 4.13 (q, 2H), 3.75 (q, 4H), 1.41 (t, 3H), 1.24 (t, 6H)

(Preparation of photosensitive resin composition)

Example  One

The photosensitive resin compositions according to Examples 1 to 3 and Comparative Examples 1 to 4 were prepared with the compositions shown in Table 1 below. Specifically, a photopolymerization initiator was dissolved in a solvent, followed by stirring at room temperature for 2 hours. To this, a binder resin and a photopolymerizable monomer were added, and the mixture was stirred at room temperature for 2 hours. The dye was added thereto (in some cases, the pigment dispersion was added), stirred at room temperature for 1 hour, and other additives (surfactant) were added and stirred at room temperature for 1 hour. The solution was filtered three times to remove impurities to prepare a photosensitive resin composition.

(Unit: wt%) Example 1 Example 2 Example 3 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 (A) Binder resin 10 10 10 10 10 10 10 (C) Photopolymerizable compound 6.5 6.5 6.5 6.5 6.5 6.5 6.5 (D) a photopolymerization initiator 0.4 0.4 0.4 0.4 0.4 0.4 0.4 (B) Colorant The dye (B-1) 33 - 20 - - 5 45 The dye (B-2) - 33 - - - - - The dye (B-3) - - - 33 - - - The pigment (B'-1) - - - - 33 - - (E) Solvent 49.8 49.8 62.8 49.8 49.8 72.8 37.8 (F) Other additives 0.3 0.3 0.3 0.3 0.3 0.3 0.3 Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0

(A) Binder resin

 (Methacrylic acid / benzyl methacrylate = 15/85 (w / w), weight average molecular weight = 22,000 g / mol, acid value = 100 mgKOH / g)

(B) Dye

 (B-1) a dye represented by the formula (7-17-1)

 (B-2) a dye represented by the formula (7-14-1)

 (B-3) a dye (Win-chemical, Brilliant Blue FG) represented by the following formula (18)

 [Chemical Formula 18]

(B ') pigment

 (B'-1) B 15: 6 Pigment dispersion (Sanyo)

(C) Photopolymerization  compound

 Dipentaerythritol hexaacrylate (DPHA)

(D) Light curing Initiator

 Oxime initiator (BASF, OXE-01)

(E) Solvent

 Propylene glycol monomethyl ether acetate (PGMEA)

(F) Other additives

 Fluorine-based surfactant (DIC, F-554 (using 10% diluent))

(evaluation)

Evaluation 1: Evaluation of luminance and heat resistance

Coating was carried out at rpm which can exhibit a certain thickness for each of the photosensitive resin compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 4 by using a coating machine (Mikasa, Opticoat MS-A150) Pre-baking (before PSB) was performed on a hot-plate at 90 ° C. Thereafter, the entire surface of the substrate was exposed using an exposure machine (Ushio, HB-50110AA) under an exposure condition of 50 mJ / cm ² , and baked at 230 ° C for 30 minutes (after PSB) under oven conditions. The color coordinates and the luminance (Y) were measured using an MCPD 3000 apparatus before and after the oven baking, and the results are shown in Table 2. The del (E *) values were calculated based on the change values before and after the PSB of the chromaticity coordinates, The results are shown in Table 3 below.

Evaluation 2: Light resistance  And chemical resistance evaluation

For the measurement of the resistance to light, the thin film specimen of Evaluation 1 was exposed for 2 hours at 60 DEG C with a xenon lamp (0.68 W intensity), and the color coordinates were measured using an MCPD 3000 apparatus. (E *) values were evaluated based on the values, and the results are shown in Table 3 below.

Evaluation 3: Chemical resistance evaluation

For measurement of the chemical resistance, the thin film specimen of Evaluation 1 was immersed in N-methylpyrrolidone (NMP) at room temperature for 10 minutes, and then taken out and dried. Thereafter, color coordinates were measured using an MCPD 3000 instrument, and the chemical resistance was evaluated by converting the color coordinate values into del (E *) values based on the change values before and after the PSB. The results are shown in Table 3 below.

Step Y Example 1 PSB I 12.12 After PSB 12.07 Example 2 PSB I 12.25 After PSB 12.18 Example 3 PSB I 12.11 After PSB 12.02 Comparative Example 1 PSB I 10.85 After PSB 10.36 Comparative Example 2 PSB I 11.31 After PSB 10.22 Comparative Example 3 PSB I 11.74 After PSB 11.20 Comparative Example 4 PSB I 10.23 After PSB 9.98

Heat resistance Light resistance Chemical resistance Example 1 1.72 1.87 2.73 Example 2 1.31 1.7 2.87 Example 3 1.45 1.83 2.78 Comparative Example 1 2.35 0.67 2.89 Comparative Example 2 4.01 11.37 20.68 Comparative Example 3 1.76 1.90 2.94 Comparative Example 4 1.99 1.92 2.98

Through the Tables 2 and 3, the photosensitive resin compositions according to Examples 1 to 3 were superior in brightness, heat resistance, and chemical resistance to the photosensitive resin compositions according to Comparative Examples 1 to 4, As shown in Fig.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

Claims (18)

(A) a binder resin;
(B) a dye consisting of a cation and an anion;
(C) a photopolymerizable compound;
(D) a photopolymerization initiator and
(E) a solvent,
The dye is contained in an amount of 10 to 40% by weight based on the total amount of the photosensitive resin composition,
Wherein the cation is represented by the following formula (1): < EMI ID =
[Chemical Formula 1]

In Formula 1,
R ¹ to R ⁶ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group,
R ⁷ is a substituted or unsubstituted C6 to C20 aryl group,
X is -O-, -S- or -NR ⁸ - (R ⁸ is a hydrogen atom, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C20 aryl group).
The method according to claim 1,
Wherein X is -O- or -S-.
The method according to claim 1,
Wherein each of R ¹ to R ⁴ is independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.
The method according to claim 1,
Wherein the cation is represented by the following formula (2): < EMI ID =
(2)

In Formula 2,
R ⁹ and R ¹⁰ are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R ¹¹ and R ¹² are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
R ¹³ is a substituted or unsubstituted C6 to C20 aryl group,
R ¹⁴ to R ¹⁷ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
n1 to n4 each independently represent an integer of 0 to 5, 0? n1 + n2? 5, 0? n3 + n4? 5,
X is -O- or -S-.
The method according to claim 1,
Wherein the cation is represented by any one of the following formulas (3) to (7).
(3)

(3)
R ¹⁸ , R ¹⁹ and R ²¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R ²² is a halogen atom,
R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
m is an integer of 0 to 2,
n5 to n8 each independently represent an integer of 0 or 1,
X is -O- or -S-)
[Chemical Formula 4]

(In the formula 4,
R ¹⁸ to R ²¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R ²² is a halogen atom,
R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
m is an integer of 0 to 2,
n5 to n8 each independently represent an integer of 0 or 1,
X is -O- or -S-)
[Chemical Formula 5]

(In the above formula (5)
R ¹⁸ and R ¹⁹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R ²² is a halogen atom,
R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R ²⁷ is a substituted or unsubstituted C6 to C20 aryl group,
m is an integer of 0 to 2,
n5 to n8 each independently represent an integer of 0 or 1,
X is -O- or -S-)
[Chemical Formula 6]

(6)
R ¹⁸ and R ¹⁹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R ²² is a halogen atom,
R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R ²⁷ and R ²⁸ are each independently a substituted or unsubstituted C6 to C20 aryl group,
m is an integer of 0 to 2,
n5 to n8 each independently represent an integer of 0 or 1,
X is -O- or -S-)
(7)

(In the above formula (7)
R ¹⁸ , R ¹⁹ and R ²¹ are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R ²² is a halogen atom,
R ²³ to R ²⁶ are each independently a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
R ²⁸ is a substituted or unsubstituted C6 to C20 aryl group,
m is an integer of 0 to 2,
n5 to n8 each independently represent an integer of 0 or 1,
X is -O- or -S-)
The method according to claim 1,
The cations are represented by the following formulas (5-3), (5-4), (5-5), (5-6), (7-6), (7-8), (7-10), (7-12) 7-17. ≪ / RTI >
[Formula 5-3]

[Formula 5-4]

[Formula 5-5]

[Formula 5-6]

[Formula 7-6]

[Formula 7-8]

[Formula 7-10]

[Formula 7-12]

[Chemical Formula 7-14]

[Formula 7-17]

The method according to claim 1,
Wherein the anion is represented by any one of the following formulas (A) to (F).
(A)

[Chemical Formula B]

≪ RTI ID = 0.0 &
PW ₁₂ O ₄₀ ^{3 -}
[Chemical Formula D]
SiW ₁₂ O ₄₀ ^{4 -}
(E)
CF ₃ SO ₃ ^-
[Chemical Formula F]
ClO ₄ ^-
The method according to claim 1,
Wherein the dye is a blue dye.
The method according to claim 1,
Wherein the dye has a maximum absorbance (? _Max ) in a wavelength range of 600 nm to 700 nm.
The method according to claim 1,
Wherein the dye has a maximum transmittance (T _max ) in a wavelength range of 400 nm to 500 nm.
The method according to claim 1,
Wherein the photosensitive resin composition further comprises a pigment.
The method according to claim 1,
The binder resin has a weight average molecular weight of 5,000 g / mol to 15,000 g / mol.
The method according to claim 1,
Wherein the binder resin has an acid value of 80 mgKOH / g to 130 mgKOH / g.
The method according to claim 1,
Wherein the binder resin comprises an acrylic binder resin, a carcass binder resin or a combination thereof.
The method according to claim 1,
The above-mentioned photosensitive resin composition is preferably used in an amount of
1 to 30% by weight of the binder resin (A);
10% to 40% by weight of the dye (B);
1 to 15% by weight of the (C) photopolymerizable compound;
0.01 to 10% by weight of the photopolymerization initiator (D)
The amount of the solvent (E)
.
The method according to claim 1,
Wherein the photosensitive resin composition further comprises an additive of an epoxy compound, malonic acid, 3-amino-1,2-propanediol, a silane coupling agent, a leveling agent, a surfactant, a radical polymerization initiator or a combination thereof.
A photosensitive resin film produced by using the photosensitive resin composition of any one of claims 1 to 16.
A color filter comprising the photosensitive resin film of claim 17.